Chemical compounds



Patented Aug. 22, 1944 2,356,682

UNITED STATES PATENT OFFICE CHEMICAL COMPOUNDS William E. Messer, Cheshire, Conn, assignor to United States Rubber Company, New York, N. Y., a. corporation of New Jersey No Drawing. Application April 30, 1942, Serial No. 441,211

2 Claims. (Cl. 260-306) This invention relates to a new class of comzothiazole and 100 cos. of carbon tetrachloride pounds which have been found valuable as accelwas added the theoretical amount of chlorine erators for the vulcanization of rubber. and this product added to 400 ccs. water, slowly,

This case is a continuation-in-part of my with strong agitation. Stirred for 2 hours pending applications Serial No. 280,929, filed June 5 more while heating to drive off solvent which 24, 1939, Patent 2,321,305, and Serial No. 334,343, may be condensed and recovered. Finally cooled filed May 10, 1940, Patent 2,321,306. with stirring and filtered off precipitate, washed The new class of compounds may be repreand. dried. Fifteen grams of a nearly white sented by the general formula R-O-X where R product are obtained having a melting range of is an arylene-thiazyl sulfide group; O is oxygen; 161-169 C. The percent nitrogen was 8.14%

and X represents an R group. (theory is 8.05% nitrogen).

These materials are derivatives of arylene- The structure is believed to be: thiazyl sulfur chloride, wherein the chlorine is N replaced by the O-X group above, when the arylene-thiazyl sulfur chloride is reacted with 5 water. During such reaction hydrogen chloride is split off. s 2

In the following illustrative examples, benzothiazyl sulfur chloride is used as the reagent; it may be prepared in solution, for purposes of reaction, by passing dry chlorine into a slurry of 1,1' dithio bisbenzothiazole in benzene, carbon tetrachloride, etc.

The following example is given to illustrate the invention in which comparison is made with a stock containing 1,1 dithio bis-benzothiazole (parts are by weight) Example s s To a mixture of 20 grams 1,1 dithio bis-ben- WILLIAM E. MESSER.

Having thus described my invention, what I claim and desire to protect by Letters Patent is:

1. A compound having the formula R-O-X where R is an arylene-thiazyl sulfide group; O is oxygen directly linked to thiol sulfur of the sulfide group; and X represents an R group.

2. A compound having the general formula 

